


Sam & the Magic Sex Toy

by brokenlittleboy



Category: Supernatural
Genre: Bottom Sam, Bottom Sam Winchester, Cursed Sam Winchester, Cursed objects, Desperate Sam Winchester, Dirty Talk, Fingerfucking, First Kiss, First Time, Fleshlights, Gencest to Realcest, Haunted Fleshlights, Jealousy, M/M, Pining, Plot What Plot/Porn Without Plot, Pre-Season/Series 01, Sex Magic, Top Dean Winchester, Trans Male Character, Trans Sam Winchester, Weecest, Weechesters, Wet & Messy
Language: English
Status: Completed
Published: 2019-08-22
Updated: 2019-08-22
Packaged: 2020-09-24 07:36:15
Rating: Explicit
Warnings: Underage
Chapters: 1
Words: 4,243
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/20354770
Author URL: https://archiveofourown.org/users/brokenlittleboy/pseuds/brokenlittleboy
Summary: Dean gets a fleshlight. Sam feels it when Dean uses it. It only gets dirtier from there.Weecest, PWP.





	Sam & the Magic Sex Toy

**Author's Note:**

  * For [kermiethefrog](https://archiveofourown.org/users/kermiethefrog/gifts).

> This is for Chris (transsammywinchester on tumblr), sorry for the wait, hope you like it!
> 
> Sam is a trans boy.
> 
> I use lots of words for anatomy, including "cunt," just FYI.

Sam’s doing his homework when Dean strides in, whistling, a bounce to his step. He’s the definition of pep and Sam groans internally. He is sure Dean has some bullshit story to tell Sam to gross him out or something.

Sure enough, Dean keeps sending Sam expectant looks, bringing up random things to get Sam to comment, all the works. Sam doesn’t play at first, but it goes on long enough that he throws down his textbook with a petulant sigh. “Dean, just spit it out, okay?”

“I went shopping,” Dean says, all giddy, and Sam hates his brain for all the stereotype-laden, Dean-esque jokes that pop into his head.

He has to bite or Dean will never let up. “Shopping for what?”

“Toys,” Dean says, leering at Sam, winking up a storm, and what the fuck Dean.

Sam makes a disgusted face. “And that’s sharing information because…?”

“Because, dorkus mcgee, I found a vintage classic.”

Before Sam can dissect that, Dean pulls a plastic box out of his shopping bag. The font is ochre and wavy and cheesy and the plastic is yellowing. The disgust on Sam’s face sours further.

“Don’t give me that look,” Dean says. “You know Amanda Bernhal?”

Unfortunately, Sam does. Amanda Bernhal was a Playboy bunny in the ‘70s or something, and both Dean and John worshipped her centerfolds. 

Their family is just as close as you’d expect from an ex-marine, and twice as gay.

Dean holds the box out so Sam can see the smiling picture of Amanda on it. Amanda and her titties and her bush. “This, right here, is an Amanda Bernhal pussy replica fleshlight. New in the box. These were only a limited run in 1974. This is probably worth thousands by now.”

Dean hands it to Sam. The plastic wrap crinkles and something shocks Sam’s palm. He almost drops it and Dean swoops in to cradle it against his chest. “Be careful with that.”

Sam rubs at his hands and tries not to look Amanda in the eyes. He wonders how old she is now.

It’s disgusting and weird, but Dean’s excitement is kind of a nice change, and Sam likes to be on the receiving end of geekery, even if said geekery has to do with pornography. He can’t help but shake his head with a little smile. “Wow. Just wow.”

Dean misinterprets his wow. “I know, right?” Sam hasn’t seen Dean smile this hard in months. “I almost want to keep it as a collector’s item. But, Sammy, if a man gets a chance to know Amanda…”

“Ugh, Dean, come on,” Sam protests, and Dean outright cackles. It makes Sam giggle, too.

“Alright, alright, alright, enough paparazzi,” Dean says with a smile. He leans in and puts a hand on Sam’s back while licking him in the ear. “Go do your homework, short squat. I got work to do!”

Dean bounces off before Sam can deck him. He holds his ear. “That’s not a real insult!” he shouts after Dean, cheeks burning, and sees a fleeting middle finger before Dean disappears into the bedroom of their little rental while Dad’s gone.

Sam has a lot of homework tonight--he’s doing well at his current school and might get switched into an honors class--and loses himself in the work. He doesn’t really mind it. It’s like research for a hunt but simpler. He enjoys learning about history and literature and science and all that. He’s not the best at math but at least it’s logical. It only takes time and patience to figure out a difficult problem, and Sam works at a challenging problem for a few hours before he can solve it with ease. He didn’t do perfectly on the last test but he’s definitely going to make up for it now.

He’s proud. He shuts the last textbook with a definitive thump, humming to himself. He cleans up his things and gets ready for school, putting a bag lunch in the fridge, his backpack by the door, and a fresh set of clothes on the dresser.

Dean’s on the bed watching T.V. when Sam picks out a pair of jeans. Dean turns the T.V. off and hops out of bed. “I’m off to work,” Dean says. “If you need me, call--”

“Call the auto line, hang up, call again,” Sam drones. “I know.”

Dean grins all cheeky. “Just checking. See you before dinner. Oh. Can you go to the store later? We’re running out of box mac and cheese.”

“Sure.”

“Seeya, Sammy.”

“Seeya, buttface.”

Dean sticks his tongue out at Sam before heading out the door. A minute later, the car engine rumbles, and Sam hears the car bump over the gravel driveway and disappear.

The moment Dean’s gone, Sam can breathe. No hair ruffling, no forced smiles, no little brother persona being annoyed at everything. He can just exist as himself with no eyes, no judgement, no expectations. He made sure to finish his work early so he can just flop around while Dean’s at work.

Dean. Dean is the problem. Not in a serious way, in a Sam’s a massive fucking idiot way.

Sam has a lot to be grateful for. John’s kind of an idiot but Dean in his own way is amazing. Dean is the one who stole him puberty blockers and now hormones. Dean is the one who fought Dad, who got Sam the clothes he wanted from Goodwill. Dean is the one who lets Sam be whatever the fuck he wants, and not some overly masculine archetype or perfect son to make up for the lost years of being called Samantha.

He’s just Sam. 

Sam has a lot to be grateful for, but he still has to go and fuck it up.

He. Uh. It’s not even fun to say because it’s weird and shameful. 

But he has a crush on Dean.

There. Urgh. Dean is literally the biggest moron Sam knows and is aggressively, disgustingly straight. Also gorgeous and older and confident and the opposite of Sam’s awkward virgin.

Also, they’re brothers.

Sam knows its wrong and he has no chance and he shouldn’t have a chance but he can’t help but pine. Pine and sigh and stare soulfully out the window and write in his diary.

Dean is so affectionate and tactile without realizing it. Dean touches Sam all the time. They’re just siblingly touches, usually gross, but Sam soaks in every single one of them and tries not to shiver or eyelash flutter when Dean touches him.

Sam has no idea why he has these feelings. He doesn’t want these feelings.

He doesn’t want them for obvious reasons, and also because they turn him into a jealous bitch.

Dean is a womanizer. Dean is drowning in pussy, now including silicone pussy. 

Often times, they’re slutty girls, they’re nice girls, they’re dominant girls, the works. 

And every time, no matter who they are, Sam hates the shit out of them.

He hates every girl who knows how to use her tits to seduce Dean. He hates every person who has ever seen Dean naked, who has touched his dick. Sam can’t help but feel like all that belongs to him, like it’s some wild breach of trust that other people have known that.

It’s making his life fucking suck. Dean is some magic wizard sex god, and this town is fairly big with fairy pretty girls, so Sam finds himself locked out with the sock on the knob and the overexaggerated moans echoing through the siding of the house more and more often.

School is a good distraction, but when he doesn’t have it, his dumb hormonal brain comes back to the same bullshit angsty thoughts. He doesn’t want to do this, he swears, but it just happens.

He perks up when he remembers Dean asked him to go to the grocery store. Maybe he can concentrate hard enough on getting all the items from a grocery list that his idiot thoughts leave him alone for a few hours. 

He writes up a list on the corner of an old receipt, tucks it into his pocket, and heads out. He unchains his bike from the chain link fence and hops on, wobbling off over gravel until he hits main street.

The Winn Dixie is quiet and old and nice and Sam likes it here. He wanders down the aisles, grabbing pasta, Kraft mac and cheese, microwave popcorn. The cashier lady tsks under her breath at his choices, but gives him an impressed look when he makes change. 

He puts the groceries in his backpack and dips. It started raining as he walked inside, and now, it’s pouring. The streets are too muddy and uneven for his bike, so he pulls up his hood and walks it back home. 

He’s only just started walking when he feels a weird warm shiver roll up from his heels to his crotch to his spine. He stumbles, frowning, pressing a hand against the small of his back. Maybe it’s the last vestige of a period, but he doesn’t think he’s ever felt something like that.

The heat bursts, like a mini explosion throughout his body, and it’s kind of pleasant, which only makes it more freaky. Sam stumbles, slowing down for a moment before speeding up, bike wheel bumping noisily against the puddles. He just needs to get home and take some meds or something. He hopes the feeling passes soon.

He’s only taken two more steps when the warm feeling slides heated and wet up and down the seam of his pussy.

Sam stops, gasping, and the feeling repeats. 

It’s really, really good, warm and wet and slow and teasing, and Sam’s the only person who’s ever been down there, and he’s been a little bit frustrated, okay, and oh my fucking god. Something swirls against his clit and it chubs up hard and fast, his pussy clenching. He’s wet before he knows it.

Sam looks up and down the street, making sure no one’s looking at him. The town is deserted.

Sam hastily locks his bike up outside the library and runs inside. He disappears into the single stall gender neutral bathroom, fingers trembling as he locks the door behind himself.

He collapses onto the toilet, wriggling out of his jeans and undies, and my god, the feeling is continuing, something rubbing him all over down there, sometimes pressing in, just barely making it past the lips, and oh my god oh my god oh my god.

He’s so wet that his thighs are shiny with it, little beads and strings of slick connecting his legs like a little bridge.

He spreads his legs wide open, leaning back against the wall and closing his eyes. His pussy clenches, wet and warm, dick hard, and he invites the feeling in.

As if things couldn’t get any crazier, the feelings reciprocate, and something bigger, more blunt, rubs at his cunt, a little rougher now, playing around in the wet, sometimes trying to push in, but he’s too tight, even as aroused as he is right now.

He bites his lip, stifling a whine, breathing labored. His eyes squeeze shut and his toes curl. He wants to touch his own dick but the feelings keep doing it for him, little teasing touches.

“Come on…” he mutters under his breath. “Come on, come on, come on…”

The blunt feeling returns, pushing, but this time, it doesn’t leave. It continues, steadily, and it hurts a little, but Sam welcomes it.

All at once, his pussy accepts the pressure, swallowing up whatever the hell this is, and Sam gasps, his heart kicking into overdrive.

It’s so goddamn good.

It’s awful how good it is. Sam always used to calm his horny, frustrated self down by reminding himself it couldn’t possibly be as good as his hormonally-driven fantasies.

It’s just as good. It’s different from how he imagined but it’s soooo gooood.

His brain has gone stupid. He bites his arm to muffle his moans.

He’s being fucked.

The wet noises are loud and gross and Sam fucking loves them.

Whatever it is pushes fully into him, stretching him wide, sitting like that for a moment before pulling out and slamming back in. Sam’s thighs shake as he’s fucked, and he moans, closing his eyes and reaching down between his legs to frantically rub at his dick.

He comes, hard, eyes rolling back, heart going fucking crazy, sweat sticking his shirt to his back, and he’s fucked through it, with an even, brutal pace, and he comes again, not from his dick but from inside, oh my god, he didn’t know he could do that.

He comes once more before the fucking gets rough and staccato and stops. The sensation remains inside his pussy long enough for him to get his breathing under control and to get his thighs to stop twitching.

The feeling withdraws, leaving Sam wet and gross and open and--

Something’s dripping. Dripping out of him.

He reaches down, fingers shaking, and when he brings them back up to his face, there’s come on his hands.

Sam lets out a breath. He pushes the fear down hard and distracts himself by cleaning himself up. With the shitty one ply toilet paper, it takes a long time, but he does it.

He pulls his pants back up, washes his hands, avoids his gaze in the mirror, and slips back out of the library.

It’s not raining anymore. He gets onto the bike very gingerly and rides home. He’s throbbing painfully.

Sam pushes through the front door, kicking off his boots and coat, and makes a beeline for the bedroom.

He walks inside and freezes.

Dean’s on the bed, naked, dick limp against his thigh, come spattering his chest, and the fleshlight is on the bed next to him. He’s out cold. 

Sam’s feet move without his permission. He makes his way to the bedside and still Dean doesn’t wake. 

He picks up the fleshlight and he already knows. He puts a thumb against the opening and feels a thumb press against his pussy.

He drops the fleshlight back on the bed and runs to the bathroom.

He locks the door behind him and stumbles over to the sink, gripping the edge hard enough to turn his nail beds white. If he shifts his hips the right way he can still feel it.

There’s no use beating around the bush. Pun intended.

He can still feel Dean’s cock.

Dean has a magic fleshlight and somehow by fucking it he fucked Sam.

And came inside him.

Sam’s like, 99% sure he can’t get pregnant, but he’s got anxiety, okay, and Dean’s come was on his fingers and some of it is probably still inside him and--

The doorknob shakes. Sam freezes. 

“Sammy?” Dean’s voice comes through the cheap plasterboard door with almost no muffle. They’re only inches apart. Dean tries the knob a second time. “Come on, I gotta piss.”

“Gimme--” Sam’s voice rattles something violent. He swallows. “Gimme a second.”

Dean knocks once on the door, and Sam hears him step away. Sam’s shoulders sag. 

He looks up at his reflection. He’ll have to buy a pregnancy test. Just to make sure.

Sam gets into the shower to clean up properly. The water is soothing and, drip by drip, he calms down. He scrubs himself thoroughly, bathroom clouding up, and lets his thoughts wander. 

As much of a mess as this whole situation is, there’s one thing he keeps coming back to.

It felt fucking amazing. Just as good as his fantasies. And all those fantasies involved Dean. And now, in a roundabout way, Sam’s fantasies have come true. He knows how Dean feels inside him. 

That thought sends a heated shiver up his spine. 

Now that he’s had it, he only wants it more.

Logically, he knows he should tell Dean at some point, sooner rather than later, or destroy the fleshlight and come up with a reasonable excuse and let Dean nurse a broken heart for a while. This cannot go on.

It cannot go on for much longer, Sam amends. 

But if Dean happens to use the fleshlight again tomorrow, well, there’s not much Sam can do about that.

When Sam leaves the bathroom, Dean’s all cleaned up and the fleshlight is out of sight. Dean looks up at him and coughs. “So.”

“So.” Sam doesn’t know what to say.

“Whatever you walked in on on your way to the bathroom…” Dean starts. He points a finger. “It’s not blackmail, right?”

Sam snorts. He walks around to the other side of the bed. “It’s Wednesday night.”

Dean sputters. Sam laughs. Dean walks over to the bathroom door, but stops by the threshold. He turns and looks back at Sam. “I haven’t scarred you too bad, have I?”

Sam rolls his eyes. “Don’t give yourself too much credit.”

Dean gives him the middle finger and disappears into the bathroom. He leaves the door open and Sam gets another glimpse at his soft cock.

Dean didn’t scar Sam. Sam did a pretty good job of that himself.

***

It turns out Sam doesn’t have to wait as long as he thought he would.

He’s only just drifted off to sleep when the mattress squeaks. He hears Dean sigh, then a box pop open. The sheets shift. Dean’s elbow bumps into him and Dean sighs again.

Sam’s expecting it, dick already waking up, and he bites the inside of his cheek when Dean’s thumb runs up and down his pussy.

Sam’s heart rabbits, and he struggles to control his breathing. Dean will stop if he realizes Sam is awake. Won’t he? Does Sam want that? Should he leave right now? Pretend to act sick?

It’s hard to make rational decisions when Dean keeps playing with him.

It’s just a toy. Dean could just push into it, dump his come, and pass out. But Dean somehow fucking loves this toy, treats it like someone’s pussy, treats it right.

And Sam is the willing recipient. 

Dean’s pace is deep and slow and good and he winds Sam up in just the right way. He establishes a rhythm with his fingers, and Sam’s eyes flutter, his toes curling.

Dean breaks the rhythm and Sam isn’t expecting it. Dean presses against the side of his clit in just the right way and Sam moans.

The finger touching him freezes and Sam freezes and Dean’s silent and Sam’s silent. Oh, fuck. Oh fuck fuck fuck fuck.

Dean’s swallow is audible. “Sammy?”

There’s still a finger on Sam. It’s not moving and it’s kind of infuriating. Sam tries to fuck up his hips to get some friction but it doesn’t work. He shakes his head and stifles a growl. “Don’t stop.”

Dean takes a moment before responding. The sheets shift. “What?”

Sam knows he’s fucking insane. Point of no return. Maybe he is cursed. Panting, he manages to say, “touch it again.”

There’s a delay but Dean fucking does it, he rubs the fleshlight’s clit. Sam moans again.

Dean laughs. It’s a sharp, disbelieving sound. “What the hell? You’re Amanda Bernhal?”

Sam whines. “Dean. Dean, please.”

Dean laughs again. “Like this?”

A finger runs from his clit to his taint. Sam’s thighs clench. He shivers. “Yes.”

Dean rubs again, pressing his finger into Sam’s wet, rubbing around just past his lips, fucking shallowly, loosening him up. “Like this?” he asks again, voice darker, deeper.

Sam’s trembling now, overheated, sweating, heart going insane, and it feels good, it feels good listening to Dean sound like that, like Dean sounds like with all the girls he brings home, and he manages another shaky “yes.”

Dean fingers him. He’s playful at first, but gets deeper, rougher, crooking his index finger inside of Sam--inside of the fleshlight, Sam needs to remember that--and rubbing at a spot that makes Sam cry out involuntarily.

Dean swears under his breath, panting with Sam. “Jesus fucking christ,” Dean says. He rubs at that spot like a man on a mission, and Sam can’t take it, it’s too much. He whimpers and whines and shakes and makes constant little needy noises until the feeling builds, his cunt bearing down hard, and ohhhh god. Sam moans through his orgasm and Dean goes crazy, rambling nonsense dirty talk and making wet noises as he beats a fist around his cock.

Sam takes a while to float back down to his body. While he does it, he listens to Dean jerk off and come. 

Dean says something to him after, but Sam’s gone. He passes out like Dean medicated him, not fingered him.

***

When Sam wakes in the morning, he’s curled up against Dean’s chest, drooling onto his pec. Dean is still asleep, Sam can tell by his deep and even breaths. They always wake like this, but Sam usually slips away before Dean can make fun of it or shift away. Sometimes Sam’s wet, sometimes Dean’s hard.

This time, they both are. 

Dean yawns, mumbling into wakefulness, blinking, and Sam takes his moment. He looks up at Dean with doe eyes. “Do it again.”

It takes Dean a moment to process what Sam’s asking for, but once he does, he wakes up, his eyes going lively, going darker. He smirks. “You sure?”

Sam nods hard enough for his hair to fall into his face.

Dean rolls onto his back, reaching onto the nightstand to grab the fleshlight. Sam turns with him, sprawled on Dean’s chest, and grabs at his wrist, stalling his movements.

“No,” Sam says. “Not with that.”

Some of Dean’s darkness waters down, the smirk thinning. “Sammy--”

“Dean,” Sam cuts him off. “I want this. Not Amanda fucking Bernhal.”

“Sammy,” Dean repeats, but it’s appraising. “You jealous?”

Before he can answer, Dean asks, “you really want this?”

Sam swallows. He bites his lip. “Have for a while.”

The darkness returns to Dean’s eyes. “Fuck,” he says. “Fuck.”

“Every time you brought a girl home, I.” Sam cuts himself off. His jaw ticks. He lifts his chin and stares defiantly up at Dean. “I can do better. Than all of them.”

Dean’s smirk turns wry. “You think?” he says. He puts a hand on Sam’s bare hip. “You wanna see?”

Sam shifts until he’s straddling Dean, thighs spread. “De,” he says. “Fuck me.”

Dean pulls Sam down until their noses brush. He bites at Sam’s lip. Sam’s body goes hot. They kiss and it’s somehow packed with all kinds of feeling and dirty and rough as all hell, leaving Sam’s lips spitty and swollen. 

Dean distracts Sam with his mouth while his hands play with Sam’s pussy. He fiddles with lips, brushes into slick, paints shapes into his dick, rubs inside and outside until Sam’s pussy is twitching and dripping onto Dean’s stomach and Sam is shaking and desperate and threatening to kill Dean unless he--

Something blunt and familiar presses against Sam. “Alright, alright,” Dean laughs. “Hold on, you brat. You’re so tiny, I don’t wanna…”

Sam reaches back, gets his hands on Dean’s cock for the first time, angles it, and sinks down on it.

He and Dean moan at the same time in the same way. Like destiny.

“Fuck,” Dean gasps. “Sammy.”

Sam rocks back, and Dean growls, getting an iron grip on Sam’s hips. “Nuh uh, we’re doing this my way,” he says, and fucks up into Sam rough and deep and oh my god. It hurts but it’s so good and he’s so wet, wetter than he’s ever been, and he’s full and the noises are so good and it’s Dean and it’s Dean and it’s Dean.

He leans forward, kissing Dean as he’s fucked. Dean sets a good pace, rocking up into Sam, and Dean gets more desperate, his noises choked off and his hips stuttering. Their kisses get uncoordinated and messy. Dean shifts just slightly and Sam cries out. He braces his thighs and throws his neck back as Dean fucks him good.

They come together, Sam sobbing, Dean groaning like he’s been stabbed. Sam feels Dean’s cock pulse inside of him as Dean comes. That’s another thing they’ll have to deal with along with the whole cursed fleshlight thing.

For now, though, Sam lets his legs go weak. He falls forward onto Dean’s chest and Dean pulls out, holding Sam close. They breathe together, just existing for a moment.

“Hey, Dean?” Sam speaks up.

“Mmm?”

“We’re gonna have to do something about Amanda, and I might need a--a test, but. I want this to stay.”

“You do, huh?”

Sam props himself up onto his elbows. “And no other girls.”

“What about Amanda?”

Sam thinks for a moment. “Amanda can stay,” he decides. “But… probably not forever.”

“Okay.” Dean is so casual. He runs a hand over Sam’s chest, just touching him, as tactile as ever, and Sam is maybe realizing something. “Okay to everything.”

Sam flops back down. “Good.” He closes his eyes.

“Hey, Sammy?” Dean says. Sam waits. Dean squeezes his ass, but it’s oddly affectionate. “I’m glad you spoke up.”

Sam can’t help a smile, eyes still closed. “Me, too.”

The next time he sleeps, it’s with Dean, through and through. When they wake, they’ll have problems to solve, things to deal with, but for now, all they think of is each other, warm skin pressed to warm skin.

The End

**Author's Note:**

> Thank you so much for reading, I hope you enjoyed the filth!
> 
> Sorry for the hiatus, more is on the way! 
> 
> <3 comments are hugs and I hug back <3


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